Find the top rated trails in Bridgeport, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The paved Charter Oak Greenway rolls more than 13 miles through the tree-covered hills and eastern suburbs of Hartford before crossing the Connecticut River and ending in the capital’s downtown. At...
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Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....
The South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
The paved Charter Oak Greenway rolls more than 13 miles through the tree-covered hills and eastern suburbs of Hartford before crossing the Connecticut River and ending in the capital’s downtown. At...
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
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Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
The Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
The Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the...
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...
The Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
The Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
The William R. Steinhaus Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....
The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
I rode the trail last week starting at the Wassaic Metro-North station (free parking only on weekends and holidays) and ending at Orphan Farm Road. I did continue to Hillsdale but as there was no signage to indicate how to find the newest section from Hillsdale to Black Grocery road, I did it on road.
All-in-all, both of the main completed sections are in very good shape, fine for road bikes. For the on road gap I took Route 22 going north (flatter but fairly busy with high-speed traffic) and the Under Mountain Road- Rudd Pond Road Route (hillier but much less traffic with swimming available at Taconic State Park- Rudd Pond) on my return. The roads were in good shape either way.
Bash Bish Falls State Park off the northern section is well worth the minor detour. Stay on the road to the falls parking lot and in a 1/4 mile (up hill) you're in Massachusetts!
They've just finished paving the trail and it's super. It's the same initial 5K of paved bike path as before, but now it continues down to River Rd and then to Grumman Blvd. You can turn north on Line Rd. to cross the site and complete the loop. 8.75 miles. The paved trail along Grumman Blvd. continues for a ways to the west beyond Line Rd., but then just stops. Perhaps they are planning to make a loop around the whole site? Or maybe they just had extra asphalt.
Dateline: Sunday July 08, 2018.
Weather: Sunny, clear, temps in the 80's, low humidity.
It has been on my list for a long time, because it's a good distance (25 miles according to my Strava) and it's only an hour drive from me. I am glad I can cross it off my list. Not in my top 5, but I many trails, so it has stiff competition. The trail itself is in pretty good shape, and no trail is perfect. The scenery to me would rate average at best, but again it has very stiff competition from the places I have visited. I definitely suggest a visit so you can decide for yourself.
Caution. After visiting many bike trails thanks to TrailLink, my only complaint is that some of the parking areas need to be reviewed more carefully. In this case I kept driving past the northern most parking area listed in Goshen and went to one midway in Monroe just off Route 17. It is a Park & Ride, very nicely paved, well lit, safe and right next to the trail.
Always take the address/directions/GPS to more than one parking lot and visit the TLink site just before departing for any updates. I drove 2.5 hours to Windsor Locks, CT to find out the entire trail was closed temporarly, and my only parking lot address closed for the entire year. But I will go back, because the trails themselves have not let me down.
Took this as an alternative to the narrow shoulder section of 9W and much like another post from last year, it's still completely overgrown - I was able to pass on 25mm tires, but it definitely wasn't easy. A ton of small rocks underneath the greenery, a fallen tree, some wet sand, etc...
The trail really has potential if it were properly maintained.
Well worth the 1 1/2 hour ride to get to!! We started at the Plainville parking area and decided to take this path to Simsbury and then return the Farmington Canal Path. The River path is beautiful and deserves the 5 stars. It runs along a beautiful river and brought us to the quaint little town of Collinsville. The only issue we had was the path came to an abrupt end at the route 202 & 44 intersection. There were no signs to indicate the street riding. Guessing , we proceeded on the street until we saw the cycling insignia. The only other poor signage is when you come out of the state forest and there is no indication until approx 100 yards that tells you that you're going in the right direction. We were glad we had the Rails to Trails Southern New England Guide Book we could keep referring to!
Pictures don’t do it justice. Get your mountain bike or cross country bike ready and hit this trail! First section of the trail is a bit busy with pedestrians, but it becomes nice and clear once you start entering the woods further north.
The trail started off great, but starlight park entry is closed and the detour is pretty far out of the way. We rode from manhattan to Bronx on bikes so we decided not to finish the trail
Would like to take this time to thank all that help keep this trail in the wonderful condition that it is in. This week was riding and notice two women picking up trash. Took time and thanked both for what they where doing. More of us should take the time when seeing these people doing work to keep this trail. Thanks !
Yes trail is paved and is great to ride smooth pavement. Was wondering why there are no entrance signs to trail. Was at Monroe, Airport Park, and there are NO MARKINGS as to where one is to enter trail. Noted small goat paths from parking lot to trail. Also was wondering why when heading South that there is no notice that trail dead ends with a chain link fence. Wonder how many law suits from hitting fence or rider dumping their bikes. Good thing that I was not goin down that hill at a fast pace, 20 plus mph. Also this trail is no way a 1. The North and South directions from Monroe are hills that are 5 degrees or more and each are 2.5 miles or longer. This would be a work out for any beginner. Just a note that I was riding a Catrike Expedition. I have about 3k miles riding trikes. Would have been nice if there was a entrance that a trike would be able to enter Trail.
August 2017
It was a great ride, next to a river, shady, smooth, and there is a parallel Farmington Canal trail that meets this one at the southern end. The north end is near a conjesting roadway and was supposed to continue on a non-paved section, but I could not find it. Go check it out.
Loved it!
Well kept, well marked bike path. Moderately traveled. All dogs I saw were on leashes. Cyclists, walkers, and runners were all very respectful of each other when passing.
I started in Bethpage State Park and went north towards Syosset. The terrain was mostly flat with a hill about 1 mile from the start (mile markers are on the pavement). It started out as mostly tree-lined and covered, but trees thinned out farther out. The path does cross major roadways, but these crossings are well marked.
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